NPASS Compound

Structure

CID265002 OpenBabel06191716062D 28 30 0 0 1 0 0 0 0 0999 V2000 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 6 0 0 0 18 24 2 0 0 0 0 18 27 1 0 0 0 0 19 25 2 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 6 0 0 0 21 27 1 6 0 0 0 22 20 1 6 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.13
Volume:	389.776
LogP:	2.467
LogD:	1.644
LogS:	-4.294
# Rotatable Bonds:	7
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	3.557
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.866
MDCK Permeability:	1.3179423149267677e-05
Pgp-inhibitor:	0.129
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.295
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.409

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.784
Plasma Protein Binding (PPB):	94.06544494628906%
Volume Distribution (VD):	0.673
Pgp-substrate:	2.787886381149292%

ADMET: Metabolism

CYP1A2-inhibitor:	0.415
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.711
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	6.442
Half-life (T1/2):	0.815

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.366
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.515
Carcinogencity:	0.394
Eye Corrosion:	0.004
Eye Irritation:	0.04
Respiratory Toxicity:	0.012

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC265002

Natural Product ID:	NPC265002
*Common Name:**	Howiinol A
IUPAC Name:	[(1R,2R)-2-hydroxy-2-[(2R,3S)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	HCJURVKKVSCZRL-VTWBULIDSA-N
Standard InCHI:	InChI=1S/C22H20O6/c23-17-12-14-19(25)28-22(17)20(26)21(16-9-5-2-6-10-16)27-18(24)13-11-15-7-3-1-4-8-15/h1-14,17,20-23,26H/b13-11+/t17-,20+,21+,22+/m0/s1
SMILES:	O=C(O[C@@H]([C@H]([C@@H]1OC(=O)C=C[C@@H]1O)O)c1ccccc1)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1170578
PubChem CID:	6440329
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9760	Goniothalamus howii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9760	Goniothalamus howii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9760	Goniothalamus howii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	900.0	nM	PMID[542355]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1100.0	nM	PMID[542355]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2600.0	nM	PMID[542355]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1600.0	nM	PMID[542355]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1500.0	nM	PMID[542355]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC265002 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	953
0.2-0.3	2322
0.3-0.4	6766
0.4-0.5	12014
0.5-0.6	11400
0.6-0.7	8026
0.7-0.8	932
0.8-0.85	35
0.85-0.9	11
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC234376
0.9423	High Similarity	NPC37115
0.9238	High Similarity	NPC472315
0.9238	High Similarity	NPC472316
0.9238	High Similarity	NPC136962
0.9238	High Similarity	NPC475203
0.9238	High Similarity	NPC474376
0.9231	High Similarity	NPC242913
0.9231	High Similarity	NPC171831
0.9231	High Similarity	NPC280616
0.9151	High Similarity	NPC277788
0.8692	High Similarity	NPC85977
0.8673	High Similarity	NPC473507
0.8649	High Similarity	NPC185840
0.8598	High Similarity	NPC234305
0.8491	Intermediate Similarity	NPC98911
0.8491	Intermediate Similarity	NPC472318
0.8482	Intermediate Similarity	NPC158282
0.8426	Intermediate Similarity	NPC91820
0.8426	Intermediate Similarity	NPC82426
0.839	Intermediate Similarity	NPC229600
0.8347	Intermediate Similarity	NPC476033
0.8347	Intermediate Similarity	NPC79608
0.8198	Intermediate Similarity	NPC477251
0.8182	Intermediate Similarity	NPC471466
0.8174	Intermediate Similarity	NPC172525
0.8173	Intermediate Similarity	NPC472319
0.8173	Intermediate Similarity	NPC119631
0.8125	Intermediate Similarity	NPC475465
0.8125	Intermediate Similarity	NPC472314
0.8108	Intermediate Similarity	NPC472919
0.8077	Intermediate Similarity	NPC240108
0.8077	Intermediate Similarity	NPC213156
0.807	Intermediate Similarity	NPC183700
0.8065	Intermediate Similarity	NPC288416
0.8	Intermediate Similarity	NPC301857
0.8	Intermediate Similarity	NPC477250
0.7984	Intermediate Similarity	NPC114096
0.7966	Intermediate Similarity	NPC470820
0.7966	Intermediate Similarity	NPC473556
0.7966	Intermediate Similarity	NPC301651
0.7946	Intermediate Similarity	NPC269457
0.7934	Intermediate Similarity	NPC470848
0.7934	Intermediate Similarity	NPC470849
0.792	Intermediate Similarity	NPC473993
0.792	Intermediate Similarity	NPC148026
0.7917	Intermediate Similarity	NPC141791
0.7917	Intermediate Similarity	NPC263386
0.7913	Intermediate Similarity	NPC63345
0.7903	Intermediate Similarity	NPC275576
0.7899	Intermediate Similarity	NPC469574
0.7895	Intermediate Similarity	NPC206341
0.7895	Intermediate Similarity	NPC184633
0.7869	Intermediate Similarity	NPC475328
0.7863	Intermediate Similarity	NPC474363
0.7863	Intermediate Similarity	NPC474641
0.785	Intermediate Similarity	NPC23453
0.7845	Intermediate Similarity	NPC474314
0.7845	Intermediate Similarity	NPC470825
0.784	Intermediate Similarity	NPC169913
0.7833	Intermediate Similarity	NPC275519
0.7826	Intermediate Similarity	NPC276061
0.7826	Intermediate Similarity	NPC474148
0.7823	Intermediate Similarity	NPC474532
0.7812	Intermediate Similarity	NPC138777
0.7812	Intermediate Similarity	NPC246869
0.7812	Intermediate Similarity	NPC108553
0.7812	Intermediate Similarity	NPC225384
0.7812	Intermediate Similarity	NPC235294
0.7812	Intermediate Similarity	NPC46137
0.7812	Intermediate Similarity	NPC478255
0.7807	Intermediate Similarity	NPC20485
0.7807	Intermediate Similarity	NPC156648
0.7807	Intermediate Similarity	NPC260952
0.7805	Intermediate Similarity	NPC325301
0.7805	Intermediate Similarity	NPC327070
0.7788	Intermediate Similarity	NPC152384
0.7788	Intermediate Similarity	NPC37714
0.7786	Intermediate Similarity	NPC471665
0.7786	Intermediate Similarity	NPC471664
0.7769	Intermediate Similarity	NPC470215
0.7769	Intermediate Similarity	NPC470214
0.7769	Intermediate Similarity	NPC886
0.7769	Intermediate Similarity	NPC109371
0.7769	Intermediate Similarity	NPC135127
0.7769	Intermediate Similarity	NPC34293
0.7769	Intermediate Similarity	NPC287597
0.7769	Intermediate Similarity	NPC477896
0.776	Intermediate Similarity	NPC45821
0.776	Intermediate Similarity	NPC126991
0.776	Intermediate Similarity	NPC83218
0.7759	Intermediate Similarity	NPC43584
0.7759	Intermediate Similarity	NPC30563
0.7759	Intermediate Similarity	NPC476003
0.7759	Intermediate Similarity	NPC323007
0.7759	Intermediate Similarity	NPC133308
0.7742	Intermediate Similarity	NPC138798
0.7742	Intermediate Similarity	NPC472373
0.7739	Intermediate Similarity	NPC281604
0.7739	Intermediate Similarity	NPC114741
0.7739	Intermediate Similarity	NPC182549
0.7727	Intermediate Similarity	NPC473301
0.7727	Intermediate Similarity	NPC154517
0.7727	Intermediate Similarity	NPC126206
0.7727	Intermediate Similarity	NPC78363
0.7724	Intermediate Similarity	NPC147654
0.7717	Intermediate Similarity	NPC225307
0.7714	Intermediate Similarity	NPC304760
0.7699	Intermediate Similarity	NPC148060
0.7698	Intermediate Similarity	NPC120225
0.7698	Intermediate Similarity	NPC213552
0.7698	Intermediate Similarity	NPC471157
0.7692	Intermediate Similarity	NPC136608
0.7692	Intermediate Similarity	NPC136994
0.7692	Intermediate Similarity	NPC88255
0.7692	Intermediate Similarity	NPC38420
0.7686	Intermediate Similarity	NPC86198
0.7686	Intermediate Similarity	NPC309434
0.768	Intermediate Similarity	NPC471758
0.7674	Intermediate Similarity	NPC233692
0.7672	Intermediate Similarity	NPC273837
0.7661	Intermediate Similarity	NPC12016
0.7661	Intermediate Similarity	NPC52097
0.7658	Intermediate Similarity	NPC80115
0.7656	Intermediate Similarity	NPC27712
0.7652	Intermediate Similarity	NPC38099
0.7652	Intermediate Similarity	NPC120852
0.7652	Intermediate Similarity	NPC26954
0.7652	Intermediate Similarity	NPC471345
0.7642	Intermediate Similarity	NPC173443
0.7642	Intermediate Similarity	NPC476872
0.7638	Intermediate Similarity	NPC58061
0.7638	Intermediate Similarity	NPC472707
0.7636	Intermediate Similarity	NPC289201
0.7634	Intermediate Similarity	NPC477893
0.7627	Intermediate Similarity	NPC290353
0.7627	Intermediate Similarity	NPC272524
0.7627	Intermediate Similarity	NPC153795
0.7627	Intermediate Similarity	NPC42911
0.7627	Intermediate Similarity	NPC128368
0.7623	Intermediate Similarity	NPC70084
0.7619	Intermediate Similarity	NPC470158
0.7619	Intermediate Similarity	NPC475933
0.7619	Intermediate Similarity	NPC289459
0.7611	Intermediate Similarity	NPC160382
0.7607	Intermediate Similarity	NPC264784
0.7603	Intermediate Similarity	NPC610
0.7603	Intermediate Similarity	NPC145023
0.7603	Intermediate Similarity	NPC175799
0.7603	Intermediate Similarity	NPC200988
0.7597	Intermediate Similarity	NPC289415
0.7597	Intermediate Similarity	NPC17567
0.7597	Intermediate Similarity	NPC319995
0.7596	Intermediate Similarity	NPC99482
0.7594	Intermediate Similarity	NPC475195
0.7594	Intermediate Similarity	NPC260425
0.7589	Intermediate Similarity	NPC42211
0.7586	Intermediate Similarity	NPC469636
0.7583	Intermediate Similarity	NPC471616
0.7583	Intermediate Similarity	NPC210531
0.7581	Intermediate Similarity	NPC11724
0.7578	Intermediate Similarity	NPC93632
0.7576	Intermediate Similarity	NPC472374
0.7576	Intermediate Similarity	NPC472372
0.7576	Intermediate Similarity	NPC476870
0.7576	Intermediate Similarity	NPC263829
0.7568	Intermediate Similarity	NPC135951
0.7565	Intermediate Similarity	NPC92623
0.7565	Intermediate Similarity	NPC135464
0.7563	Intermediate Similarity	NPC87069
0.7563	Intermediate Similarity	NPC307651
0.7563	Intermediate Similarity	NPC153053
0.7561	Intermediate Similarity	NPC243059
0.7561	Intermediate Similarity	NPC280827
0.7559	Intermediate Similarity	NPC476972
0.7559	Intermediate Similarity	NPC252114
0.7559	Intermediate Similarity	NPC476971
0.7559	Intermediate Similarity	NPC61181
0.7559	Intermediate Similarity	NPC118584
0.7557	Intermediate Similarity	NPC28836
0.7557	Intermediate Similarity	NPC311492
0.7556	Intermediate Similarity	NPC152771
0.7556	Intermediate Similarity	NPC195357
0.7556	Intermediate Similarity	NPC134405
0.7556	Intermediate Similarity	NPC476385
0.7542	Intermediate Similarity	NPC139946
0.7542	Intermediate Similarity	NPC321852
0.7541	Intermediate Similarity	NPC254233
0.7541	Intermediate Similarity	NPC203124
0.754	Intermediate Similarity	NPC246704
0.754	Intermediate Similarity	NPC469568
0.754	Intermediate Similarity	NPC57607
0.754	Intermediate Similarity	NPC246166
0.7538	Intermediate Similarity	NPC239358
0.7537	Intermediate Similarity	NPC64141
0.7537	Intermediate Similarity	NPC328273
0.7537	Intermediate Similarity	NPC472350
0.7537	Intermediate Similarity	NPC100913
0.7537	Intermediate Similarity	NPC279573
0.7537	Intermediate Similarity	NPC151946

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC265002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	680
0.2-0.3	1337
0.3-0.4	2637
0.4-0.5	2391
0.5-0.6	1385
0.6-0.7	486
0.7-0.8	33
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8034	Intermediate Similarity	NPD4198	Discontinued
0.7851	Intermediate Similarity	NPD5125	Phase 3
0.7851	Intermediate Similarity	NPD5126	Approved
0.7845	Intermediate Similarity	NPD969	Suspended
0.7797	Intermediate Similarity	NPD2629	Approved
0.7667	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5909	Discontinued
0.7537	Intermediate Similarity	NPD7266	Discontinued
0.7519	Intermediate Similarity	NPD5454	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1238	Approved
0.746	Intermediate Similarity	NPD7876	Discontinued
0.7456	Intermediate Similarity	NPD6647	Phase 2
0.7411	Intermediate Similarity	NPD9495	Approved
0.7391	Intermediate Similarity	NPD1237	Approved
0.7373	Intermediate Similarity	NPD2067	Discontinued
0.7355	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7798	Approved
0.7328	Intermediate Similarity	NPD5048	Discontinued
0.7311	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1282	Approved
0.7288	Intermediate Similarity	NPD2182	Approved
0.7287	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7258	Intermediate Similarity	NPD7741	Discontinued
0.7252	Intermediate Similarity	NPD7008	Discontinued
0.7246	Intermediate Similarity	NPD4628	Phase 3
0.7209	Intermediate Similarity	NPD2797	Approved
0.7203	Intermediate Similarity	NPD1358	Approved
0.7197	Intermediate Similarity	NPD6798	Discontinued
0.7194	Intermediate Similarity	NPD6190	Approved
0.7164	Intermediate Similarity	NPD4340	Discontinued
0.7155	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5926	Approved
0.709	Intermediate Similarity	NPD4060	Phase 1
0.7087	Intermediate Similarity	NPD4135	Approved
0.7087	Intermediate Similarity	NPD3496	Discontinued
0.7087	Intermediate Similarity	NPD4136	Approved
0.7087	Intermediate Similarity	NPD4106	Approved
0.7073	Intermediate Similarity	NPD5951	Approved
0.7068	Intermediate Similarity	NPD3268	Approved
0.7068	Intermediate Similarity	NPD2313	Discontinued
0.7049	Intermediate Similarity	NPD5535	Approved
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.7031	Intermediate Similarity	NPD6287	Discontinued
0.7015	Intermediate Similarity	NPD4404	Approved
0.7009	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5306	Approved
0.7008	Intermediate Similarity	NPD5305	Approved
0.7007	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD689	Discontinued
0.7	Intermediate Similarity	NPD3225	Approved
0.7	Intermediate Similarity	NPD2684	Approved
0.7	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3027	Phase 3
0.6992	Remote Similarity	NPD7095	Approved
0.6985	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6653	Approved
0.6983	Remote Similarity	NPD2549	Approved
0.6983	Remote Similarity	NPD2550	Approved
0.6983	Remote Similarity	NPD2553	Approved
0.6983	Remote Similarity	NPD2555	Approved
0.6983	Remote Similarity	NPD2552	Approved
0.6983	Remote Similarity	NPD2558	Approved
0.6975	Remote Similarity	NPD3134	Approved
0.6975	Remote Similarity	NPD6685	Approved
0.6963	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD164	Approved
0.6944	Remote Similarity	NPD5403	Approved
0.6942	Remote Similarity	NPD5237	Approved
0.6942	Remote Similarity	NPD5235	Approved
0.6942	Remote Similarity	NPD5236	Approved
0.6942	Remote Similarity	NPD5239	Approved
0.6942	Remote Similarity	NPD5240	Approved
0.694	Remote Similarity	NPD3764	Approved
0.6929	Remote Similarity	NPD4102	Approved
0.6929	Remote Similarity	NPD1652	Phase 2
0.6929	Remote Similarity	NPD4105	Approved
0.6923	Remote Similarity	NPD4189	Approved
0.6923	Remote Similarity	NPD4188	Approved
0.6923	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4380	Phase 2
0.6917	Remote Similarity	NPD4620	Approved
0.6917	Remote Similarity	NPD5201	Approved
0.6917	Remote Similarity	NPD4617	Approved
0.6917	Remote Similarity	NPD290	Approved
0.6917	Remote Similarity	NPD5203	Approved
0.6912	Remote Similarity	NPD5124	Phase 1
0.6912	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7843	Approved
0.6903	Remote Similarity	NPD1202	Approved
0.6901	Remote Similarity	NPD7236	Approved
0.6899	Remote Similarity	NPD1091	Approved
0.6899	Remote Similarity	NPD4807	Approved
0.6899	Remote Similarity	NPD4480	Approved
0.6899	Remote Similarity	NPD4806	Approved
0.6897	Remote Similarity	NPD2066	Phase 3
0.6889	Remote Similarity	NPD4062	Phase 3
0.6884	Remote Similarity	NPD4308	Phase 3
0.688	Remote Similarity	NPD7157	Approved
0.6875	Remote Similarity	NPD5723	Approved
0.6875	Remote Similarity	NPD6516	Phase 2
0.6875	Remote Similarity	NPD5846	Approved
0.687	Remote Similarity	NPD5667	Approved
0.6864	Remote Similarity	NPD5765	Approved
0.6864	Remote Similarity	NPD1929	Approved
0.6864	Remote Similarity	NPD1930	Approved
0.6864	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6010	Discontinued
0.685	Remote Similarity	NPD1894	Discontinued
0.6846	Remote Similarity	NPD5402	Approved
0.6842	Remote Similarity	NPD5204	Approved
0.6838	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1613	Approved
0.6835	Remote Similarity	NPD2935	Discontinued
0.6835	Remote Similarity	NPD6032	Approved
0.6833	Remote Similarity	NPD968	Approved
0.6833	Remote Similarity	NPD3524	Approved
0.6833	Remote Similarity	NPD3526	Approved
0.6831	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD9294	Approved
0.6822	Remote Similarity	NPD3847	Discontinued
0.6812	Remote Similarity	NPD5886	Approved
0.6812	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4536	Approved
0.6812	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7097	Phase 1
0.6812	Remote Similarity	NPD41	Approved
0.6812	Remote Similarity	NPD4538	Approved
0.6807	Remote Similarity	NPD3047	Approved
0.6807	Remote Similarity	NPD3046	Approved
0.6807	Remote Similarity	NPD3048	Approved
0.6806	Remote Similarity	NPD5401	Approved
0.6791	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5762	Approved
0.6786	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5763	Approved
0.6786	Remote Similarity	NPD9258	Approved
0.6786	Remote Similarity	NPD9256	Approved
0.6783	Remote Similarity	NPD2859	Approved
0.6783	Remote Similarity	NPD1989	Approved
0.6783	Remote Similarity	NPD2860	Approved
0.6781	Remote Similarity	NPD1653	Approved
0.6777	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6085	Phase 2
0.6767	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5960	Phase 3
0.6763	Remote Similarity	NPD5588	Approved
0.6761	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD8166	Discontinued
0.6759	Remote Similarity	NPD3971	Phase 1
0.6755	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3020	Approved
0.675	Remote Similarity	NPD9697	Approved
0.6744	Remote Similarity	NPD4626	Approved
0.6744	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2424	Discontinued
0.6735	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD9545	Approved
0.6715	Remote Similarity	NPD5119	Approved
0.6715	Remote Similarity	NPD4140	Approved
0.6715	Remote Similarity	NPD6309	Approved
0.6715	Remote Similarity	NPD5121	Approved
0.6715	Remote Similarity	NPD6311	Approved
0.6715	Remote Similarity	NPD6310	Approved
0.6715	Remote Similarity	NPD5120	Approved
0.6711	Remote Similarity	NPD6801	Discontinued
0.6696	Remote Similarity	NPD2934	Approved
0.6696	Remote Similarity	NPD2933	Approved
0.6694	Remote Similarity	NPD2559	Approved
0.6694	Remote Similarity	NPD2551	Approved
0.6694	Remote Similarity	NPD6912	Phase 3
0.6693	Remote Similarity	NPD5292	Approved
0.6693	Remote Similarity	NPD9493	Approved
0.6693	Remote Similarity	NPD5291	Approved
0.6692	Remote Similarity	NPD1203	Approved
0.6692	Remote Similarity	NPD2159	Approved
0.6692	Remote Similarity	NPD2625	Approved
0.6692	Remote Similarity	NPD3266	Approved
0.6692	Remote Similarity	NPD2626	Approved
0.6692	Remote Similarity	NPD3267	Approved
0.6692	Remote Similarity	NPD2627	Approved
0.6692	Remote Similarity	NPD2628	Approved
0.6692	Remote Similarity	NPD2160	Approved
0.669	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5157	Phase 1
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD5159	Phase 2
0.6667	Remote Similarity	NPD3021	Approved
0.6667	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7239	Suspended
0.6667	Remote Similarity	NPD3022	Approved
0.6645	Remote Similarity	NPD7075	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data